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Playing media through Cloudflare fails: "The video did not start playing in time"

I'm trying to proxy requests to my server through Cloudflare (HTTPS), as the direct peering from some locations to my server is very slow. This works fine with Plex Web, Plex for iOS and Plex for Android.
When using the PS4 Client (1.40), browsing the library works fine, but playing an item results in the error "There was a problem playing this item. The video did not start playing in time."

This is mostly a bug in PS4's client. It sort of works if you enable port 80, and disable HSTS and other forms of automatic http->https redirects. However, it doesn't work with cloudflare (even if you disable those things on cloudflare). PS4 is able to see the server, and get the metadata, but it won't actually play anything.

Report it to the Plex devs, if you need PS4 support you'll have to disable CF nothing I can really do to help fix this. Out of my control, sorry folks

I just realized that you don't even have to disable remote access. Even when the server is reachable on the default port 32400, specifying the Cloudflare URL in the "Custom server access URLs" will make the PS4 app fail to play anything.

Yeah. Running Cloudflare with Plex will cause the PS4 app to not play media content. The PS4 app is in a pretty dismal state at the moment overall. Not sure if just difficult to develop for or what but it's definitely unfortunate

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